Novel surfactant-like hypocrellin derivatives to achieve simultaneous drug delivery in blood plasma and cell uptake

Photochemistry and Photobiology

Volumn 86, Issue 3, 2010, Pages 667-672

  Zhang, Yang ^a   Song, Liming ^a   Xie, Jie ^a   Qiu, Haixia ^b   Gu, Ying ^b   Zhao, Jingquan ^a  

^a INSTITUTE OF CHEMISTRY   (China)

^b CHINESE PLA GENERAL HOSPITAL   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; DRUG DERIVATIVE; FREE RADICAL; HYPOCRELLIN A; HYPOCRELLIN B; PERYLENE; PHOTOSENSITIZING AGENT; QUINONE DERIVATIVE; REACTIVE OXYGEN METABOLITE;

ARTICLE; BLOOD; BREAST TUMOR; CHEMISTRY; DRUG DELIVERY SYSTEM; HUMAN; HYDROPHOBICITY; METABOLISM; METHODOLOGY; PHOTOCHEMOTHERAPY; SOLUBILITY; SYNTHESIS; ANALOGS AND DERIVATIVES; BREAST NEOPLASMS; CHEMICAL PHENOMENA; PROCEDURES;

ANTINEOPLASTIC AGENTS; BLOOD; BREAST NEOPLASMS; DRUG DELIVERY SYSTEMS; FREE RADICALS; HUMANS; HYDROPHOBICITY; PERYLENE; PHOTOCHEMOTHERAPY; PHOTOSENSITIZING AGENTS; QUINONES; REACTIVE OXYGEN SPECIES; SOLUBILITY; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS;

EID: 77951866380     PISSN: 00318655     EISSN: 17511097     Source Type: Journal    
DOI: 10.1111/j.1751-1097.2010.00711.x     Document Type: Article

References (49)

1. Henderson, B. W. T. J. Dougherty (1992) How does photodynamic therapy work? Photochem. Photobiol. 55, 145 157.
2. Dougherty, T. J., C. J. Gomer, B. W. Henderson, G. Jori, D. Kessel, M. Korbelik, J. Moan Q. Peng (1998) Photodynamic therapy. J. Natl Cancer Inst. 90, 889 905. (Pubitemid 28304157)
3. Wang, K., Y. Gu, F. G. Liu, J. Liang, Y. M. Pan, J. Zeng X. Y. Tong (2003) Clinical analysis of 238 cases of port wine stains patients treated by HMME-PDT. Chin. J. Aesthetic. Med. 12, 476 478.
4. Incorvaia, C., C. Campa, F. Parmeggiani, M. Menzione, S. D'angelo, M. Della Corte, M. Rinaldi, M. Romano, R. Dell'omo C. Costagliola (2008) 12-month retrospective study and review of photodynamic therapy with verteporfin for subfoveal choroidal neovascularization in age-related macular degeneration. Retina. J. Retinal. Vitreous Dis. 28, 289 297. (Pubitemid 351643160)
5. Maziak, D. E., B. R. Markman, J. A. Mackay, W. K. Evans Cancer Care Ontario Practice Guidelines Initiative Lung Cancer Disease Site Group (2004) Photodynamic therapy in nonsmall cell lung cancer: A systematic review. Ann. Thor. Surg. 77, 1484 1491. (Pubitemid 38452417)
6. Maunoury, V., S. Mordon, P. Bulois, X. Mirabel, B. Hecquet C. Mariette (2005) Photodynamic therapy for early oesophageal cancer. Dig. Liver Dis. 37, 491 495. (Pubitemid 44356064)
7. Braathen, L. R., R. M. Szeimies, N. Basset-Seguin, R. Bissonnette, P. Foley, D. Pariser, R. Roelandts, A. M. Wennberg C. A. Morton (2007) Guidelines on the use of photodynamic therapy for nonmelanoma skin cancer: An international consensus. J. Am. Acad. Dermatol. 56, 125 143. (Pubitemid 44969292)
8. Oldewarris, J. V. P. Retel (2007) Photodynamic therapy, a new treatment modality in head and neck cancer. Ejc. Suppl. 5, 443.
9. Juarranz, A., P. Jaen, F. Sanz-Rodriguez, J. Cuevas S. Gonzalez (2008) Photodynamic therapy of cancer. Basic principles and applications. Clin. Trans. Oncol. 10, 148 154.
10. Miller, G. G., K. Brown, A. M. Ballangrud, O. Barajas, Z. Xiao, J. Tulip, J. W. Lown, J. M. Leithoff, M. J. Allalunis-Turner, R. D. Mehta R. B. Moore (1997) Preclinical assessment of hypocrellin B and hypocrellin B derivatives as sensitizers for photodynamic therapy of cancer: Progress update. Photochem. Photobiol. 65, 714 722. (Pubitemid 27210658)
11. Xu, S. J., S. Chen, M. H. Zhang, T. Shen, Y. P. Zhao, Z. W. Liu Y. D. Wu (2001) Butylamino-demethoxy-hypocrellins and photodynamic therapy decreases human cancer in vitro and in vivo. BBA. Mol. Basis. 1537, 222 232. (Pubitemid 33139804)
12. Lee, H. Y., Z. X. Zhou, S. Chen, M. H. Zhang T. Shen (2006) New long-wavelength ethanolamino-substituted hypocrellin: Photodynamic activity and toxicity to MGC803 cancer cell. Dyes Pigm. 68, 1 10. (Pubitemid 40473605)
13. Hu, Y. Z., J. Y. An, L. J. Jiang L. C. Chiang (1993) Studies of the sulfonation of hypocrellin-A and the photodynamic actions of the product. J. Photochem. Photobiol. B, Biol. 17, 195 201.
14. Hu, Y. Z., J. Y. An L. C. Chiang (1993) Studies on the photoinduced sulfonation of hypocrellins. J. Photochem. Photobiol. A, Chem. 70, 301 308.
15. 2). Free Radic. Biol. Med. 27, 203 213.
16. He, Y. Y., J. Y. An L. J. Jiang (1999) Glycoconjugated hypocrellin: Synthesis of [(beta-d-glucosyl)ethylthiyl]hypocrellins and photosensitized generation of singlet oxygen. BBA. Gen. Subjects 1472, 232 239.
17. He, Y. Y., J. Y. An, W. Zou L. J. Jiang (1998) Photoreactions of hypocrellin B with thiol compounds. J. Photochem. Photobiol. B, Biol. 44, 45 52. (Pubitemid 28423126)
18. He, Y. Y., J. Y. An L. J. Jiang (1999) Synthesis of a new water-soluble phototherapeutic sensitizer from hypocrellin B with enhanced red absorption. Dyes Pigm. 41, 93 100.
19. Ou, Z. Z., J. R. Chen, X. S. Wang, B. W. Zhang Y. Cao (2002) Synthesis of a water-soluble cyclodextrin modified hypocrellin and ESR study of its photodynamic therapy properties. New J. Chem. 26, 1130 1136. (Pubitemid 35034645)
20. He, Y. Y., H. Y. Liu, J. Y. An, R. Han L. J. Jiang (1999) Photodynamic action of hypocrellin dyes: Structure-activity relationships. Dyes Pigm. 44, 63 67. (Pubitemid 30499056)
21. An, J. Y., L. J. Jiang K. H. Zhao (1992) The reduction and nucleophilic addition of mercaptoethanol to hypocrellin A. Chin. Sci. Bull. 37, 1274 1279.
22. Weng, M., M. H. Zhang, L. Ma, T. Shen L. J. Jiang (1997) New long-wavelength perylenequinones. The reaction between hypocrellin B and mercapto compounds. Dyes Pigm. 35, 297 310. (Pubitemid 127347528)
23. Song, Y. Z., J. Y. An L. J. Jiang (1999) ESR studies of the photodynamic properties of a long-wavelength and water-soluble hypocrellin B derivative: Photogeneration of semiquinone radical anion and activated oxygen. J. Photochem. Photobiol. A, Chem. 123, 39 46.
24. Tang, Y. J., H. Y. Liu, J. Y. An R. Han (2001) Synthesis, characterization and photodynamic activity of amino-substituted hypocrellin derivatives. Photochem. Photobiol. 74, 201 205.
25. He, Y. Y. L. J. Jiang (2000) Synthesis and EPR investigations of new aminated hypocrellin derivatives. Free Radic. Biol. Med. 28, 1642 1651.
26. Diwu, Z. J., R. P. Haugland, J. X. Liu, J. W. Lown, G. G. Miller, R. B. Moore, K. Brown, J. Tulip M. S. Mcphee (1996) Photosensitization by anticancer agents. 21. New perylene- and aminonaphthoquinones. Free Radic. Biol. Med. 20, 589 593. (Pubitemid 26097276)
27. Li, L., Y. W. Chen, J. Q. Shen, M. H. Zhang T. Shen (2000) New long-wavelength perylenequinones: Synthesis and phototoxicity of hypocrellin B derivatives. BBA. Gen. Subjects. 1523, 6 12.
28. Xu, S. J., S. Chen, M. Zhang T. Shen (2001) A novel method for the preparation of amino-substituted hypocrellin B. Bioorg. Med. Chem. Lett. 11, 2045 2047. (Pubitemid 32709721)
29. Xu, S. J., S. Chen, M. H. Zhang, T. Shen, Z. W. Liu, Y. P. Zhao Y. D. Wu (2001) Cyclohexylamino-demethoxy-hypocrellin B and photodynamic therapy decreases human cancer in vitro. Anti-Cancer Drug Des. 16, 271 277. (Pubitemid 33139804)
30. Xu, S. J., S. Chen, M. H. Zhang T. Shen (2003) Synthesis, characterization and photodynamic activity of phenmethylamino-demethoxy- hypocrellin B. J. Photochem. Photobiol. B, Biol. 72, 61 67. (Pubitemid 37509036)
31. Xu, S. J., S. Chen, M. H. Zhang T. Shen (2004) Hypocrellin derivative with improvements of red absorption and active oxygen species generation. Bioorg. Med. Chem. Lett. 14, 1499 1501. (Pubitemid 38299437)
32. Zhao, Y. W. J. Q. Zhao (2004) Preparation of a novel hypocrellin derivative and its photochemical, photophysical properties. Dyes Pigm. 63, 175 179.
33. Xu, S. J., S. Chen, M. H. Zhang, T. Shen, X. X. Zhang Z. P. Wang (2003) Synthesis and characterization of three novel amphiphilic aminated hypocrellins as photodynamic therapeutic agents. Photochem. Photobiol. 78, 411 415.
34. g). J. Photochem. Photobiol. B, Biol. 71, 43 50. (Pubitemid 37258830)
35. Zeng, Z., R. Qiao, J. Zhou, S. Xia, Y. Zhang, Y. Liu, J. Chen, X. Wang B. Zhang (2007) Photodynamic properties of dipeptide-modified hypocrellin B derivatives: The role of tyrosine and tryptophan groups. J. Phys. Chem. B 111, 3742 3749. (Pubitemid 46724003)
36. Zhao, K. H. L. J. Jiang (1989) Conversion of hypocrellin A in alkaline and neutral media. Youji Huaxue. 9, 252 254.
37. Diwu, Z. J. J. W. Lown (1992) Photosensitization by anticancer agents. 12. Perylene quinonoid pigments, a novel type of singlet oxygen sensitizer. J. Photochem. Photobiol. A, Chem. 64, 273 287.
38. Fisher, A. M. R., K. Danenberg, D. Banerjee, J. R. Bertino, P. Danenberg C. J. Gomer (1997) Increased photosensitivity in HL60 cells expressing wild-type p53. Photochem. Photobiol. 66, 265 270. (Pubitemid 127470176)
39. Hu, Y. Z., J. Y. An, L. J. Jiang D. W. Chen (1995) Spectroscopic study on the photoreduction of hypocrellin A: Generation of semiquinone radical anion and hydroquinone. J. Photochem. Photobiol. A, Chem. 89, 45 51.
40. Eichler, J., J. Knof H. Lenz (1977) Measurements on depth of penetration of light (0.35-1.0 μM) in tissue. Radiat. Environ. Biophys. 14, 239 242. (Pubitemid 8190620)
41. Hu, Y. Z., J. Y. An, L. Qin L. J. Jiang (1994) Studies of the triplet state properties of hypocrellin A by nanosecond flash photolysis. J. Photochem. Photobiol. B, Biol. 78, 247 251.
42. 2) by hypocrellin B in TX-100 micelles microsurroundings. Free Radical Res. 37, 1107 1112. (Pubitemid 37265333)
43. Zhao, Y. W., H. Xie J. Q. Zhao (2005) The photosensitization activity of a water-soluble carboxylate of hypocrellin B. Dyes Pigm. 66, 61 68.
44. Zhao, Y. W., J. Xie, J. S. Ma J. Q. Zhao (2004) A novel amphiphilic 2-taurine substituted hypocrellin B (THB) and its photodynamic activity. New J. Chem. 28, 484 489. (Pubitemid 38570071)
45. Liu, X., J. Xie, L. Y. Zhang, H. X. Chen, Y. Gu J. Q. Zhao (2009) A novel hypocrellin B derivative designed and synthesized by taking consideration to both drug delivery and biological photodynamic activity. J. Photochem. Photobiol. B, Biol. 94, 171 178.
46. He, Y. Y., J. Y. An L. J. Jiang (1999) Effect of structural modifications on the photosensitized activities of hypocrellin dyes: EPR and spectrophotometric studies. Free Radic. Biol. Med. 26, 1146 1157.
47. Lion, Y., M. Delmelle A. Vandevorst (1976) New method of detecting singlet oxygen production. Nature 263, 442 443.
48. 2 and ̇OH) during the photosensitization of a water-soluble perylenequinone derivative. J. Photochem. Photobiol. B, Biol. 33, 51 59. (Pubitemid 26160078)
49. Liu, H. L., F. G. Liu, Y. Gu, J. H. Ma, J. Q. Zhao, J. Zeng X. S. Li (2005) An experimental study of photodynamic effect of hypocrelline B liposome on leghorn cock comb. Chin. J. Laser. Med. Surg. 14, 1 5.